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Dimethylformamide → N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

HRID 2064056
Notes
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Reaction equation

HRID 2064056 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C.CN(C)C=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:24][CH:21]2[CH2:20][CH2:19][N:18]([CH:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[CH2:23][CH2:22]2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 225621451-(Tetrahydro-2H-pyran-4-yl)piperidin-4-amine

Product 1

HCID 59863010N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
200 °C

Procedure

400 mg (0.0018 mol, 1 eq) of 4-bromo-2-fluoro-1-nitro-benzene, 330 mg (0.0018 mol, 1 eq) of D9, 350 mg (0.0027 mol, 1.5 eq) of diisopropylethylamine, and 5 mL of dimethylformamide were combined, heated to 200° C. and held for 1 min in a microwave reactor. 80 mL of water was then added and the reaction extracted with 2×75 mL of dichloromethane. The dichloromethane layers were combined, dried with sodium sulfate, and evaporated to yield N-(5-bromo-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine which was used without further purification in the next step. MS (ESI): 385 [M+H]+.

Workup

  1. extractionthe reaction extracted with 2×75 mL of dichloromethane
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-bd917dc650ec40149d8330ea22309810
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes